(E)-3-(4-Fluoro­phen­yl)-1-phenyl-2-propen-1-one

Jing, L.-H.

doi:10.1107/S1600536809037635

organic compounds

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ISSN: 2056-9890

Volume 65| Part 10| October 2009| Page o2515

doi:10.1107/S1600536809037635

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(E)-3-(4-Fluorophenyl)-1-phenyl-2-propen-1-one

Lin-Hai Jing ^a ^*

^aSchool of Chemistry and Chemical Engineering, China West Normal University, Nanchong 637002, People's Republic of China
^*Correspondence e-mail: jlhjhr@yahoo.com.cn

(Received 16 September 2009; accepted 17 September 2009; online 26 September 2009)

In the title compound, C₁₅H₁₁FO, the configuration of the keto group with respect to the olefinic double bond is s–cis. The dihedral angle between the planes of the two benzene rings is 10.61 (10)°. The crystal packing is stabilized by C—H⋯π interactions involving both benzene rings.

Related literature

For the synthesis, see: Chimenti et al. (2008 ). For the biological activity of chalcone derivatives, see: Dimmock et al. (1999 ).

Experimental

Crystal data

C₁₅H₁₁FO
M_r = 226.24
Monoclinic, C c
a = 24.926 (9) Å
b = 5.6940 (19) Å
c = 7.749 (3) Å
β = 94.747 (5)°
V = 1096.0 (6) Å³
Z = 4
Mo Kα radiation
μ = 0.10 mm⁻¹
T = 93 K
0.40 × 0.33 × 0.30 mm

Data collection

Rigaku SPIDER diffractometer
Absorption correction: none
4214 measured reflections
1256 independent reflections
1174 reflections with I > 2σ(I)
R_int = 0.027

Refinement

R[F² > 2σ(F²)] = 0.032
wR(F²) = 0.066
S = 1.05
1256 reflections
154 parameters
2 restraints
H-atom parameters constrained
Δρ_max = 0.20 e Å⁻³
Δρ_min = −0.14 e Å⁻³

Table 1
Hydrogen-bond geometry (Å, °)

D—H⋯A	D—H	H⋯A	D⋯A	D—H⋯A
C1—H1⋯Cg1ⁱ	0.95	2.89	3.592 (3)	132
C4—H4⋯Cg1ⁱⁱ	0.95	2.93	3.646 (6)	133
C12—H12⋯Cg2ⁱⁱⁱ	0.95	2.85	3.505 (8)	127
Symmetry codes: (i) $[x+{\script{1\over 2}}, y+{\script{5\over 2}}, z]$ ; (ii) $[x+{\script{1\over 2}}, y+{\script{3\over 2}}, z-1]$ ; (iii) $[x+{\script{1\over 2}}, y+{\script{1\over 2}}, z-1]$ . Cg1 and Cg2 are the centroids of the C1–C6 and C10–C15 rings, respectively.

Data collection: RAPID-AUTO (Rigaku/MSC, 2004 ); cell refinement: RAPID-AUTO; data reduction: RAPID-AUTO; program(s) used to solve structure: SHELXS97 (Sheldrick, 2008 ); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97.

Supporting information

Crystal structure: contains datablocks global, I. DOI: 10.1107/S1600536809037635/ci2914sup1.cif

Structure factors: contains datablock I. DOI: 10.1107/S1600536809037635/ci2914Isup2.hkl

checkCIF report

Comment top

Chalcone derivatives are a class of important compounds that possess antiprotzoal, antihelmintic, amoebicidal, anti-ulcer, antiviral, insecticidal, antibacterial, anticancer, cytotoxic and immunosuppressive activities (Dimmock et al., 1999). The author reports here the crystal structure of the title compound, a chalocone derivative.

Bond lengths and angles in the title molecule (Fig.1) are normal. The configuration of the keto group with respect to the olefinic double bond is s-cis, with a O1—C7—C8—C9 torsion angle of -7.1 (3)°. The C1-C6 and C10-C15 benzene rings form a dihedral angle of 10.61 (10)°.

The crystal packing is stabilized by C—H···π interactions involving both benzene rings (Table 1; Cg1 and Cg2 are centroids of the C1-C6 and C10-C15 rings, respectively).

Related literature top

For the synthesis, see: Chimenti et al. (2008). For the biological activity of chalcone derivatives, see: Dimmock et al. (1999).

Experimental top

The title compound was synthesized according to the method reported in the literature (Chimenti et al., 2008). Colourless single crystals suitable for X-ray diffraction were obtained by slow evaporation of a acetone solution of the compound.

Computing details top

Data collection: RAPID-AUTO (Rigaku/MSC, 2004); cell refinement: RAPID-AUTO (Rigaku/MSC, 2004); data reduction: RAPID-AUTO (Rigaku/MSC, 2004); program(s) used to solve structure: SHELXS97 (Sheldrick, 2008); program(s) used to refine structure: SHELXL97 (Sheldrick, 2008); molecular graphics: XP in SHELXTL (Sheldrick, 2008); software used to prepare material for publication: SHELXL97 (Sheldrick, 2008).

Figures top

Fig. 1. The molecular structure of the title compound, showing 50% probability displacement ellipsoids and the atomic numbering.

(E)-3-(4-Fluorophenyl)-1-phenyl-2-propen-1-one top

Crystal data top

C₁₅H₁₁FO	F(000) = 472
M_r = 226.24	D_x = 1.371 Mg m⁻³
Monoclinic, Cc	Mo Kα radiation, λ = 0.71073 Å
Hall symbol: C -2yc	Cell parameters from 1803 reflections
a = 24.926 (9) Å	θ = 3.2–27.5°
b = 5.6940 (19) Å	µ = 0.10 mm⁻¹
c = 7.749 (3) Å	T = 93 K
β = 94.747 (5)°	Block, colourless
V = 1096.0 (6) Å³	0.40 × 0.33 × 0.30 mm
Z = 4

Data collection top

Rigaku SPIDER diffractometer	1174 reflections with I > 2σ(I)
Radiation source: Rotating anode	R_int = 0.027
Graphite monochromator	θ_max = 27.5°, θ_min = 3.3°
ω scans	h = −32→32
4214 measured reflections	k = −7→6
1256 independent reflections	l = −10→9

Refinement top

Refinement on F²	Primary atom site location: structure-invariant direct methods
Least-squares matrix: full	Secondary atom site location: difference Fourier map
R[F² > 2σ(F²)] = 0.032	Hydrogen site location: inferred from neighbouring sites
wR(F²) = 0.066	H-atom parameters constrained
S = 1.05	w = 1/[σ²(F_o²) + (0.02P)² + 0.6P] where P = (F_o² + 2F_c²)/3
1256 reflections	(Δ/σ)_max = 0.010
154 parameters	Δρ_max = 0.20 e Å⁻³
2 restraints	Δρ_min = −0.14 e Å⁻³

Crystal data top

C₁₅H₁₁FO	V = 1096.0 (6) Å³
M_r = 226.24	Z = 4
Monoclinic, Cc	Mo Kα radiation
a = 24.926 (9) Å	µ = 0.10 mm⁻¹
b = 5.6940 (19) Å	T = 93 K
c = 7.749 (3) Å	0.40 × 0.33 × 0.30 mm
β = 94.747 (5)°

Data collection top

Rigaku SPIDER diffractometer	1174 reflections with I > 2σ(I)
4214 measured reflections	R_int = 0.027
1256 independent reflections

Refinement top

R[F² > 2σ(F²)] = 0.032	2 restraints
wR(F²) = 0.066	H-atom parameters constrained
S = 1.05	Δρ_max = 0.20 e Å⁻³
1256 reflections	Δρ_min = −0.14 e Å⁻³
154 parameters

Special details top

Geometry. All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell e.s.d.'s are taken into account individually in the estimation of e.s.d.'s in distances, angles and torsion angles; correlations between e.s.d.'s in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s. planes.

Refinement. Refinement of F² against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F², conventional R-factors R are based on F, with F set to zero for negative F². The threshold expression of F² > σ(F²) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F² are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger.

Fractional atomic coordinates and isotropic or equivalent isotropic displacement parameters (Å²) top

	x	y	z	U_iso*/U_eq
F1	0.78252 (5)	−0.0769 (2)	0.41272 (15)	0.0283 (3)
O1	0.54146 (6)	0.8936 (3)	0.5750 (2)	0.0298 (4)
C1	0.43870 (9)	0.9349 (4)	0.4181 (3)	0.0201 (5)
H1	0.4526	1.0584	0.4912	0.024*
C2	0.38614 (9)	0.9458 (4)	0.3436 (3)	0.0224 (5)
H2	0.3642	1.0767	0.3660	0.027*
C3	0.36564 (8)	0.7667 (4)	0.2369 (3)	0.0220 (5)
H3	0.3296	0.7749	0.1868	0.026*
C4	0.39742 (9)	0.5758 (4)	0.2026 (3)	0.0222 (5)
H4	0.3834	0.4539	0.1282	0.027*
C5	0.45022 (9)	0.5632 (4)	0.2780 (3)	0.0205 (5)
H5	0.4720	0.4315	0.2555	0.025*
C6	0.47111 (8)	0.7420 (4)	0.3855 (3)	0.0180 (4)
C7	0.52705 (8)	0.7380 (4)	0.4726 (3)	0.0205 (4)
C8	0.56390 (9)	0.5435 (4)	0.4363 (3)	0.0217 (5)
H8	0.5512	0.4142	0.3669	0.026*
C9	0.61504 (8)	0.5513 (4)	0.5016 (3)	0.0199 (4)
H9	0.6250	0.6836	0.5718	0.024*
C10	0.65773 (9)	0.3806 (4)	0.4783 (3)	0.0185 (4)
C11	0.64836 (9)	0.1657 (4)	0.3938 (3)	0.0214 (5)
H11	0.6127	0.1239	0.3526	0.026*
C12	0.69023 (9)	0.0130 (4)	0.3692 (3)	0.0225 (5)
H12	0.6838	−0.1310	0.3091	0.027*
C13	0.74170 (9)	0.0754 (4)	0.4343 (3)	0.0211 (5)
C14	0.75290 (8)	0.2834 (4)	0.5203 (3)	0.0212 (4)
H14	0.7886	0.3216	0.5635	0.025*
C15	0.71063 (9)	0.4355 (4)	0.5420 (3)	0.0207 (4)
H15	0.7176	0.5799	0.6012	0.025*

Atomic displacement parameters (Å²) top

	U¹¹	U²²	U³³	U¹²	U¹³	U²³
F1	0.0222 (7)	0.0284 (7)	0.0342 (8)	0.0079 (6)	0.0022 (5)	0.0009 (6)
O1	0.0228 (8)	0.0330 (9)	0.0326 (9)	0.0047 (7)	−0.0034 (7)	−0.0121 (8)
C1	0.0228 (11)	0.0192 (11)	0.0185 (11)	−0.0002 (9)	0.0021 (8)	−0.0011 (9)
C2	0.0221 (11)	0.0227 (11)	0.0227 (11)	0.0043 (9)	0.0032 (9)	0.0017 (9)
C3	0.0177 (10)	0.0265 (11)	0.0218 (11)	0.0006 (9)	0.0017 (9)	0.0031 (9)
C4	0.0218 (11)	0.0232 (11)	0.0215 (11)	−0.0036 (9)	0.0012 (8)	−0.0011 (9)
C5	0.0218 (11)	0.0205 (11)	0.0196 (10)	0.0027 (9)	0.0046 (9)	0.0002 (9)
C6	0.0177 (10)	0.0206 (11)	0.0161 (10)	0.0007 (8)	0.0031 (8)	0.0028 (8)
C7	0.0187 (10)	0.0230 (11)	0.0199 (10)	0.0001 (9)	0.0026 (8)	0.0005 (9)
C8	0.0228 (10)	0.0215 (11)	0.0206 (10)	0.0014 (9)	0.0012 (8)	−0.0019 (9)
C9	0.0209 (10)	0.0209 (11)	0.0178 (10)	0.0023 (9)	0.0012 (8)	−0.0003 (9)
C10	0.0179 (10)	0.0210 (10)	0.0163 (10)	0.0021 (9)	0.0004 (8)	0.0033 (9)
C11	0.0177 (10)	0.0249 (11)	0.0211 (11)	−0.0018 (9)	−0.0013 (8)	0.0021 (9)
C12	0.0247 (11)	0.0222 (11)	0.0206 (11)	0.0014 (9)	0.0012 (9)	0.0005 (9)
C13	0.0191 (11)	0.0229 (11)	0.0217 (12)	0.0047 (9)	0.0040 (8)	0.0042 (9)
C14	0.0155 (10)	0.0259 (11)	0.0218 (10)	−0.0017 (9)	−0.0005 (8)	0.0030 (10)
C15	0.0214 (11)	0.0204 (10)	0.0199 (11)	−0.0005 (9)	−0.0009 (8)	0.0004 (9)

Geometric parameters (Å, º) top

F1—C13	1.358 (2)	C8—C9	1.333 (3)
O1—C7	1.223 (3)	C8—H8	0.95
C1—C2	1.389 (3)	C9—C10	1.463 (3)
C1—C6	1.399 (3)	C9—H9	0.95
C1—H1	0.95	C10—C11	1.398 (3)
C2—C3	1.384 (3)	C10—C15	1.404 (3)
C2—H2	0.95	C11—C12	1.383 (3)
C3—C4	1.384 (3)	C11—H11	0.95
C3—H3	0.95	C12—C13	1.386 (3)
C4—C5	1.397 (3)	C12—H12	0.95
C4—H4	0.95	C13—C14	1.376 (3)
C5—C6	1.389 (3)	C14—C15	1.385 (3)
C5—H5	0.95	C14—H14	0.95
C6—C7	1.498 (3)	C15—H15	0.95
C7—C8	1.481 (3)

C2—C1—C6	119.9 (2)	C7—C8—H8	120.3
C2—C1—H1	120.0	C8—C9—C10	127.8 (2)
C6—C1—H1	120.0	C8—C9—H9	116.1
C3—C2—C1	120.3 (2)	C10—C9—H9	116.1
C3—C2—H2	119.8	C11—C10—C15	118.37 (19)
C1—C2—H2	119.8	C11—C10—C9	122.95 (19)
C2—C3—C4	120.3 (2)	C15—C10—C9	118.68 (19)
C2—C3—H3	119.8	C12—C11—C10	121.0 (2)
C4—C3—H3	119.8	C12—C11—H11	119.5
C3—C4—C5	119.6 (2)	C10—C11—H11	119.5
C3—C4—H4	120.2	C11—C12—C13	118.4 (2)
C5—C4—H4	120.2	C11—C12—H12	120.8
C6—C5—C4	120.43 (19)	C13—C12—H12	120.8
C6—C5—H5	119.8	F1—C13—C14	119.03 (19)
C4—C5—H5	119.8	F1—C13—C12	118.19 (19)
C5—C6—C1	119.37 (19)	C14—C13—C12	122.8 (2)
C5—C6—C7	123.20 (18)	C13—C14—C15	118.11 (19)
C1—C6—C7	117.42 (18)	C13—C14—H14	120.9
O1—C7—C8	120.79 (19)	C15—C14—H14	120.9
O1—C7—C6	119.56 (19)	C14—C15—C10	121.3 (2)
C8—C7—C6	119.64 (18)	C14—C15—H15	119.3
C9—C8—C7	119.4 (2)	C10—C15—H15	119.3
C9—C8—H8	120.3

C6—C1—C2—C3	−0.1 (3)	C7—C8—C9—C10	−178.7 (2)
C1—C2—C3—C4	−0.3 (3)	C8—C9—C10—C11	−6.7 (3)
C2—C3—C4—C5	0.7 (3)	C8—C9—C10—C15	172.6 (2)
C3—C4—C5—C6	−0.6 (3)	C15—C10—C11—C12	−1.7 (3)
C4—C5—C6—C1	0.2 (3)	C9—C10—C11—C12	177.7 (2)
C4—C5—C6—C7	179.0 (2)	C10—C11—C12—C13	1.6 (3)
C2—C1—C6—C5	0.2 (3)	C11—C12—C13—F1	178.78 (19)
C2—C1—C6—C7	−178.7 (2)	C11—C12—C13—C14	−0.8 (3)
C5—C6—C7—O1	−175.0 (2)	F1—C13—C14—C15	−179.54 (18)
C1—C6—C7—O1	3.9 (3)	C12—C13—C14—C15	0.0 (3)
C5—C6—C7—C8	4.0 (3)	C13—C14—C15—C10	−0.1 (3)
C1—C6—C7—C8	−177.2 (2)	C11—C10—C15—C14	0.9 (3)
O1—C7—C8—C9	−7.1 (3)	C9—C10—C15—C14	−178.5 (2)
C6—C7—C8—C9	174.0 (2)

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ⁱ	0.95	2.89	3.592 (3)	132
C4—H4···Cg1ⁱⁱ	0.95	2.93	3.646 (6)	133
C12—H12···Cg2ⁱⁱⁱ	0.95	2.85	3.505 (8)	127

Symmetry codes: (i) x+1/2, y+5/2, z; (ii) x+1/2, y+3/2, z−1; (iii) x+1/2, y+1/2, z−1.

Experimental details

Crystal data
Chemical formula	C₁₅H₁₁FO
M_r	226.24
Crystal system, space group	Monoclinic, Cc
Temperature (K)	93
a, b, c (Å)	24.926 (9), 5.6940 (19), 7.749 (3)
β (°)	94.747 (5)
V (Å³)	1096.0 (6)
Z	4
Radiation type	Mo Kα
µ (mm⁻¹)	0.10
Crystal size (mm)	0.40 × 0.33 × 0.30

Data collection
Diffractometer	Rigaku SPIDER diffractometer
Absorption correction	–
No. of measured, independent and observed [I > 2σ(I)] reflections	4214, 1256, 1174
R_int	0.027
(sin θ/λ)_max (Å⁻¹)	0.649

Refinement
R[F² > 2σ(F²)], wR(F²), S	0.032, 0.066, 1.05
No. of reflections	1256
No. of parameters	154
No. of restraints	2
H-atom treatment	H-atom parameters constrained
Δρ_max, Δρ_min (e Å⁻³)	0.20, −0.14

Computer programs: RAPID-AUTO (Rigaku/MSC, 2004), SHELXS97 (Sheldrick, 2008), SHELXL97 (Sheldrick, 2008), XP in SHELXTL (Sheldrick, 2008).

Hydrogen-bond geometry (Å, º) top

D—H···A	D—H	H···A	D···A	D—H···A
C1—H1···Cg1ⁱ	0.95	2.89	3.592 (3)	132
C4—H4···Cg1ⁱⁱ	0.95	2.93	3.646 (6)	133
C12—H12···Cg2ⁱⁱⁱ	0.95	2.85	3.505 (8)	127

Symmetry codes: (i) x+1/2, y+5/2, z; (ii) x+1/2, y+3/2, z−1; (iii) x+1/2, y+1/2, z−1.

Acknowledgements

The author thanks the Centre for Testing and Analysis, Cheng Du Branch, Chinese Academy of Sciences, for analytical support.

References

Chimenti, F., Fioravanti, R., Bolasco, A., Manna, F., Chimenti, P., Secci, D., Rossi, F., Turini, P., Ortuso, F., Alcaro, S. & Cardia, M. C. (2008). Eur. J. Med. Chem. 43, 2262–2267. Web of Science CrossRef PubMed CAS Google Scholar
Dimmock, J. R., Elias, D. W., Beazely, M. A. & Kandepu, N. M. (1999). Curr. Med. Chem. 6, 1125–1149. Web of Science PubMed CAS Google Scholar
Rigaku/MSC (2004). RAPID-AUTO. Rigaku/MSC Inc., The Woodlands, Texas, USA. Google Scholar
Sheldrick, G. M. (2008). Acta Cryst. A64, 112–122. Web of Science CrossRef CAS IUCr Journals Google Scholar